Hostname: page-component-78c5997874-fbnjt Total loading time: 0 Render date: 2024-11-16T07:28:16.346Z Has data issue: false hasContentIssue false
  • English
  • Français

Highly efficient phase transfer catalyst supported on Janus composite particles: Synthesis, characterization, and applications

Published online by Cambridge University Press:  20 June 2014

Qinhui Chen ,
Longhui Zheng ,
Baoling Chen ,
Junhui He ,
Haibin Huang  and
Jinhuo Lin
Qinhui Chen*
Affiliation:
College of Material Science and Engineering, Fujian Normal University, Fuzhou 350007, China; and Fujian Key Laboratory of Polymer Materials, Fuzhou 350007, China
Longhui Zheng
Affiliation:
College of Material Science and Engineering, Fujian Normal University, Fuzhou 350007, China
Baoling Chen*
Affiliation:
College of Material Science and Engineering, Fujian Normal University, Fuzhou 350007, China
Junhui He*
Affiliation:
College of Material Science and Engineering, Fujian Normal University, Fuzhou 350007, China
Haibin Huang
Affiliation:
College of Material Science and Engineering, Fujian Normal University, Fuzhou 350007, China
Jinhuo Lin
Affiliation:
College of Material Science and Engineering, Fujian Normal University, Fuzhou 350007, China; and Fujian Key Laboratory of Polymer Materials, Fuzhou 350007, China
*
a) Address all correspondence to this author. e-mail: [email protected]
Get access

Abstract

Groups of chloromethyl were randomly grafted to Janus composite particles and quaternization was carried out on the particles. The Janus material of titania–quaternary ammoniated poly(vinylbenzyl chloride–divinylbenzene) (TiO2–QApoly(VBC–DVB)) was investigated in detail. Results revealed that the anisotropic Janus material containing quaternary ammonium groups was synthesized successfully. The Janus material could be used as the phase transfer catalyst. The catalytic activity of the Janus material was confirmed by the esterification reaction of benzyl chloride and sodium acetate. In the presence of 0.5 wt.% (relative to benzyl chloride) of TiO2–QApoly(VBC–DVB), the esterification yield of benzyl acetate reached 87.6% when the molar ratio of sodium acetate anhydrous to benzyl chloride was 1.2. The catalyst exhibited a high activity and had no obvious loss of activity when recycled three times. Moreover, the Janus material was easily recovered by centrifugation and washed with ethanol and water.

Keywords

catalyticpolymercomposite
Type
Articles
Information
Journal of Materials Research , Volume 29 , Issue 11 , 14 June 2014 , pp. 1231 - 1236
Copyright
Copyright © Materials Research Society 2014 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

de Gennes, P.G.: Soft matter. Rev. Mod. Phys. 64(3), 645–648 (1992).Google Scholar
Walther, A. and Muller, A.H.E.: Janus particles. Soft Matter 4(4), 663–668 (2008).Google Scholar
Chen, Q., Li, Q., and Lin, J.: Synthesis of Janus composite particles by the template of dumbbell-like silica/polystyrene. Mater. Chem. Phys. 128(3), 377–382 (2011).Google Scholar
Liu, B., Liu, J., Liang, F., Wang, Q., Zhang, C., Qu, X., Li, J., Qiu, D., and Yang, Z.: Robust anisotropic composite particles with tunable Janus balance. Macromolecules 45(12), 5176–5184 (2012).Google Scholar
Zhao, L., Zhu, L., Chen, Y., Wang, Q., Li, J., Zhang, C., Liang, F., Qu, X., and Yang, Z.: Janus micro-reactors. Chem. Commun. 49(55), 6161–6163 (2013).Google Scholar
Zheng, L., Chen, Q., Chen, B., and Lin, J.: Swelling synthesis and modification of Janus composite particles containing natural urushiol. Mater. Lett. 120, 271–274 (2014).CrossRefGoogle Scholar
Shah, R.K., Kim, J.W., and Weitz, D.A.: Janus supraparticles by induced phase separation of nanoparticles in droplets. Adv. Mater. 21(19), 1949–1953 (2009).CrossRefGoogle Scholar
Hu, J., Zhou, S., Sun, Y., Fang, X., and Wu, L.: Fabrication, properties and applications of Janus particles. Chem. Soc. Rev. 41(11), 4356–4378 (2012).Google Scholar
Knauer, A., Csáki, A., Fritzsche, W., Serra, C.A., Leclerc, N., and Michael Köhler, J.: Micro continuous flow-through synthesis of triangular silver nanoprisms and their incorporation in complexly composed polymer microparticles. Chem. Eng. J. 227, 191–197 (2013).Google Scholar
Yin, Y., Zhou, S., You, B., and Wu, L.: Facile fabrication and self-assembly of polystyrene-silica asymmetric colloid spheres. J. Polym. Sci., Part A: Polym. Chem. 49(15), 3272–3279 (2011).Google Scholar
McConnell, M.D., Kraeutler, M.J., Yang, S., and Composto, R.J.: Patchy and multiregion Janus particles with tunable optical properties. Nano Lett. 10(2), 603–609 (2010).Google Scholar
Sun, Y., Chen, M., Wang, Z., and Wu, L.: Facile synthesis of asymmetric Ag-organosilica hybrid nanoparticles with tunable morphologies and optical properties. Chem. Commun. 50(43), 5767–5770 (2014).CrossRefGoogle ScholarPubMed
Ning, Y., Wang, C., Ngai, T., and Tong, Z.: Fabrication of tunable Janus microspheres with dual anisotropy of porosity and magnetism. Langmuir 29(17), 5138–5144 (2013).Google Scholar
Liang, F., Shen, K., Qu, X., Zhang, C., Wang, Q., Li, J., Liu, J., and Yang, Z.: Inorganic Janus nanosheets. Angew. Chem. Int. Ed. 50(10), 2379–2382 (2011).CrossRefGoogle ScholarPubMed
Chen, Y., Liang, F., Yang, H., Zhang, C., Wang, Q., Qu, X., Li, J., Cai, Y., Qiu, D., and Yang, Z.: Janus nanosheets of polymer–inorganic layered composites. Macromolecules 45(3), 1460–1467 (2012).CrossRefGoogle Scholar
Lee, K.J., Hwang, S., Yoon, J., Bhaskar, S., Park, T.H., and Lahann, J.: Compartmentalized photoreactions within compositionally anisotropic Janus microstructures. Macromol. Rapid Commun. 32(5), 431–437 (2011).Google Scholar
Yoon, J., Lee, K.J., and Lahann, J.: Multifunctional polymer particles with distinct compartments. J. Mater. Chem. 21(24), 8502–8510 (2011).Google Scholar
Tang, C., Zhang, C., Sun, Y., Liang, F., Wang, Q., Li, J., Qu, X., and Yang, Z.: Janus anisotropic hybrid particles with tunable size from patchy composite spheres. Macromolecules 46(1), 188–193 (2013).Google Scholar
Chen, Q., Chen, B., Zheng, L., and Lin, J.: Preparation of polyaniline/polystyrene Janus composite particles. Chem. J. Chinese Univ. 34(7), 1788–1793 (2013).Google Scholar
Khalaf, H.I. and Hasan, O.A.: Effect of quaternary ammonium salt as a phase transfer catalyst for the microwave depolymerization of polyethylene terephthalate waste bottles. Chem. Eng. J. 192, 45–48 (2012).CrossRefGoogle Scholar
Jew, S.S. and Park, H.G.: Cinchona-based phase-transfer catalysts for asymmetric synthesis. Chem. Commun. (Camb). (46), 7090–7103 (2009).Google Scholar
Enders, D. and Nguyen, T.V.: Chiral quaternary phosphonium salts: A new class of organocatalysts. Org. Biomol. Chem. 10(28), 5327–5331 (2012).Google Scholar
Thompson, L.A. and Ellman, J.A.: Synthesis and applications of small molecule libraries. Chem. Rev. 96(1), 555–600 (1996).Google Scholar
Chen, Z.X., Xu, G.Y., Yang, G.C., and Wang, W.: Preparation of non-cross-linked polystyrene-supported quaternary ammonium salts and use as phase transfer catalysts under microwave. React. Funct. Polym. 61(1), 139–146 (2004).Google Scholar
Neumann, R. and Cohen, M.: Solvent-anchored supported liquid phase catalysis: Polyoxometalate-catalyzed oxidations. Angew. Chem. Int. Ed. 36(16), 1738–1740 (1997).Google Scholar
Annunziata, R., Benaglia, M., Cinquini, M., Cozzi, F., and Tocco, G.: A poly(ethylene glycol)-supported quaternary ammonium salt: an efficient, recoverable, and recyclable phase-transfer catalyst. Org. Lett. 2(12), 1737–1739 (2000).CrossRefGoogle Scholar
Crossley, S., Faria, J., Shen, M., and Resasco, D.E.: Solid nanoparticles that catalyze biofuel upgrade reactions at the water/oil interface. Science 327(5961), 68–72 (2010).Google Scholar
Lv, W., Lee, K.J., Li, J., Park, T.H., Hwang, S., Hart, A.J., Zhang, F., and Lahann, J.: Anisotropic Janus catalysts for spatially controlled chemical reactions. Small 8(20), 3116–3122 (2012).Google Scholar
Chen, Q.H., Zheng, L.H., Chen, B.L., and Lin, J.H.: Scalable synthesis of TiO2–Ag Janus composite particles. Eur. Polym. J. 49(9), 2610–2616 (2013).Google Scholar
Gao, B., Wang, L., Du, R., and Li, Y.: Synthesis of N‐butylphthalimide catalyzed by quaternary phosphonium salt‐type triphase catalysts based on cross‐linked polystyrene microspheres. Int. J. Chem. Kinet. 43(12), 677–686 (2011).CrossRefGoogle Scholar
Hongjie, L. and Zhang, L.: An overview on synthetic methods of benzyl acetate. Eur. Chem. Bull. 2(5), 272–274 (2013).Google Scholar
Tang, C., Zhang, C., Liu, J., Qu, X., Li, J., and Yang, Z.: Large scale synthesis of Janus submicrometer sized colloids by seeded emulsion polymerization. Macromolecules 43(11), 5114–5120 (2010).Google Scholar